The Brilliant Bass
by katoloveforever
Summary: NY 1922, the tempo of the city had changed sharply, the buildings were higher, the parties were bigger, the morals were looser and the liquor was cheaper. Chuck Bass a womanizing billionaire. Blair Walforf a wealthy socialite engaged to Carter Baizen . He finds her alluring, she finds him intriguing. Will it ever work out between them when all is against? Rated T. WILL change to M


**AN: I know I should not be posting yet another story since I have other 3 to complete but this is just calling to me. I live Gossip Girl and The Great Gatsby so as I rewatched the show finale I saw how Dan Humphrey was right making the analogy between TGG and GG (The Upper East Side(rs)) and I completely agreed so I decided to create this story I will be posting the entire summer. I am not going anywhere so I can write all the time.**

**xoxo Kato**

**The Brilliant Bass**

**Narrator POV:**

A certain young man strutted through Manhattan with a determined glint in his eye. His long strides marked a pace only few could catch up to, metaphorically speaking of course. He was the youngest billionaire in the world. He was the most desired of men. The most popular of celebrities, if you could call a simple business man a celebrity. But no, this was no simple man; there was nothing simple about him. He of course was Chuck Bass.

**Chuck POV:**

Walking through the crowded streets I look for that place. I may still be new to the city but I certainly know where to be and who to meet, I am _the_ Chuck Bass aren't I? I walk towards the barber shop on 75th **(I've only been to NY twice so I'm just making up random addresses)** and as I walk in, I look around carefully, wouldn't want anyone knowing my new club is behind this _barber shop_. Oh no, Victrola is for the classy elite, not the fake new money that is suddenly appearing in everyone's hands. Some may think that Victrola was a prestigious gentlemen's club, not really, women could come as long as they were the ones who accompanied said gentlemen of course.

I nodded curtly to the barbers who helped keep the disguise. Then walked to the back wall and knocked on the framed picture of a boat, the small window behind was opened immediately. One of my men took a quick look at me and opened the door discreetly without any hesitation.

"Mr. Bass, good to see you."

"Yes Oliver, good to see you too, is Mr. Archibald here yet?" I answered him.

"Yes Mr. Bass, he's over there at the table to the far left of the stage." Oliver dutifully pointed to the table.

"Perfect."

I silently strutted to Nathaniel "Nate" Archibald, an old friend of mine who also happened to live next to my family's old home, my new home now. As I approached his table I saw that there were two other people with him, a man and a woman from the looks of it, although through the dim lighting I couldn't see their faces very well. Men ripped their gazes from my show girls to shake my hand and greet me.

"Nathaniel, old sport!" I called out as I neared his table.

"Charles!" He cried out in surprise as he rose from the table to greet me.

It was then that the woman with whom he was talking to turned around and I saw _her._

With a perfect hourglass figure, perfectly sized breasts, thick, luscious brown curls, flawless ivory skin, plump, rosy lips and rich brown eyes that captivated you. She was stunning. Perfect for my record. Yes, my record, I Chuck Bass, am the most notorious womanizer in all of New York, with women tripping over themselves to just get your attention you become quite popular and skillful in the bedroom, _if you know what I mean. _

"Nathaniel, who is this lovely lady here?" I asked Nate, never taking my eyes off the beautiful woman before my eyes.

"_This lady_, Chuck, is my cousin Blair Waldorf. From my mother's side." Nate answered with a small grin and a knowing look.

It was then when she carefully stood up with a small smile and gave out left hand to be properly greeted. I took her small, dainty hand and leaned down to kiss her knuckles that I noticed the enormous diamond ring on her finger.

"Ms. Waldorf, Chuck Bass, pleasure to meet you." I said while letting go of her hand.

"Pleasure to meet you too Mr. Bass." She said in a velvety smooth voice, a small smirk playing on her lips and a mischevious glint in her eyes.

"Please call me Chuck, congratulations on your engagement by the way." I told her. I was certainly disappointed to say the least, to find out she's engaged, I would have loved to have taken her to my bed any time. She looked like an angel, so gorgeous.

"And Chuck, this is Carter, Blair's fiancé." Nate told me while looking at the man.

He stepped out of the shadows and rage filled me, why was this bastard inside my club?! And he's this gorgeous woman's fiancé?! This bastard should be in jail, not enjoying the pleasures of life, and certainly not in my club. Carter Baizen and I go way back, he and I used to be pals back in the day when I was about 14 years old, nine years ago. But he betrayed me, stole from me and left me drugged in an alley after we had an argument six years ago when I was just 17 and he was 19. Even though I am already nearing my 23rd birthday, I still haven't forgotten the way he stole from me, lied to my face and made a ridicule of me in front of my already disgusted father. You see, my father hated me because back when we were poor, my mother got pregnant with me and died giving birth to me due to some birthing complications, my father couldn't pay for a doctor and blamed me for taking the love of his life away. Carter just made our already strained relationship worse, we only talk in business meetings since then.

"Chuck, good to see you again." He exclaimed cheerfully with an arrogant, smug smile on his face and a teasing look in his eyes.

"Baizen, never a pleasure." I spat out through gritted teeth.

"Woah there Bass, why so mean? Mistress didn't show last night?" Carter teased.

Just as I was about to kill the guy for being a complete asshole, someone took care of him much faster.

"Carter! Don't be rude! You are welcome to sleep in the guest room tonight, I will not tolerate you being so distasteful and rude in front of me!" Blair exclaimed indignantly.

"Blair-"

"No Carter, we're only a monh away from our wedding and it is time you start acting like a grown up, I will not tolerate any discurtesies towards anyone from you. Understood?" Blair exclaimed, stainding up face to face with Carter.

"I-" Carter began.

"CARTER!" She reprimanded with a fierce look in her eyes.

"Yes dear." Carter said quietly with a humilliated and reprimanded look on his face.

Nate and I were stunned to say the least, both with our brows so far up, they looked like part of our hair. I for one, had never seen a woman stand up to a man, and even less to a man like Carter Baizen.

"Now, I am leaving to the house because one, I have things to do with Serena, Dorota and my mother about the wedding and two, I can't stand this place, the morals are looser than a a button on a homeless man's coat." Blair calmly told Carter as she grabbed her coat and purse from her chair.

I couldn't keep my eyes off this beauty. Said lady excused herself and left Victrola quicker than whiskey heats up your body.

"Well Baizen, you have found yourself a fine fine lady." I teased Carter with a smirk on my face.

"What do you mean by that Bass?!" Carter responded angrily, rounding up on me.

"I mean that she looks like a beauty with enough brains to know that you are an animal and she treats you _just_ like one." I told him while grabbing a scotch passing on a waiter's tray.

I was barely putting the rim of the glass to my lips when someone unexpected spoke.

"Yeah, you wouldn't believe. No wonder she's the one and only woman in the world that attends Yale. **(Btw, I know that the first woman admitted into Yale was in 1969, but let's pretend it's Blair in 1922)**." Nate said smugly.

"Wait! What?!" I asked Nate in shock. _SHE_ was the imfamous girl who was able to get into Yale for the first time in history?!

"What you heard Bass, and she's all mine." Carter sneered as he too took a scotch from a passing waiter's tray.

"Oh please Baizen, if I tried, she would be mine in less than five minutes and in my bed in less than two." I sneered back, tipping the whole glass of scotch. The bitter taste leaving my mouth and traveling smoothly down my throat.

"I doubt it Bass, she's not interested in womanizing pigs like yourself. She would never even look twice your way." Carter told me smugly, nursing his scotch.

"Then do explain why she even looked your way, you may be the only person worse than me." I told him with narrowed eyes, I couldn't let this fucker win.

"Bass, there is a difference, I at least have tried to make myself a little better to say the least, she likes me because I have the money, the looks, the charm and I have servants attending to her every need in the mansion I bought her on the bay of _East Egg. _I give her everything and she was attracted to that." Carter boasted smugly.

"Oh Baizen, if you'd like I could give your lady a try. Let her see that there is much _much_ better in the world than _you._" I told Carter, spitting out the word you as if it was the most digusting word ever.

"Don't you dare approach her, you are bad news Bass." Carter threatened me with a fierce look in his eyes.

"Oh, have I touched a sore spot? You only tell me to stay away because you know I would win her in seconds." I told him with a smug smirk on my face.

"No. I am telling you to stay away because you are not good for her, or for anyone while we're at it." Carter told me defensively. A little to defensive at that.

"Well then, if you are not afraid, prove it by bringing her to a party in my house. _The Empire_as people call my great mansion, you may have heard that I throw the best parties in all of the East Coast. Bring her to one of my parties tomorrow and you may have your pride back." I challenged him with a smug smirk on my face and a teasing glint in my eyes.

"Fine-" Carter started, but I of course being me, interrupted him.

"But keep this in mind Carter, I will not back off of Blair, she will be in my bed, moaning my name in ecstasy, one way or another. She will be under me writhing in pleasure. I will not back off, I intend to have my way with the gorgeous Blair Waldorf and show her that there are much better choices than you." I told him seriously.

"Don't you dare touch her Bass. She's mine and _only _mine. Her virginity is mine as well." Carter spat possesively.

"Virginity you say?" I told him interestedly.

"W-"

"So she's a virgin? My my Baizen,just wehn I was losing interest you made it peak. She hasn't had sex with you? Or anyone at that matter? But here's the thing, she hasn't had sex with you, so whatever you are doing must not be enough for a lady like her." I teased him. A virgin huh?This should be fun.

"Shut up Bass!" Carter seethed.

"Don't get your panties in a twist old sport." I nearly laughed.

"Fine, we'll do it your way Bass. I am not afraid of you. See you tomorrow." Carter told me as he grabbed his stuff and left Victrola.

"Chuck, what have you gotten yourself into?" Nate asked with a tired expression etched on his face.

"Nathaniel, I have no idea."

**Yei! First chapter is done :) if you got here it is because you liked it. I'll try to upload the next chapter later today or early tomorrow.**

**I DO NOT OWN GOSSIP GIRL OR THE GREAT GATSBY SADLY :(.**

**xoxo Kato**


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